Thiazole → 2-Biphenyl-4-yl-1-(1,3-thiazol-2-yl)ethanone

HRID 449494Notes

Reaction equation

HRID 449494 reaction equation
C([Mg]Cl)(C)C.[S:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.[C:11]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:16]=[CH:15][C:14]([CH2:17][C:18](N(OC)C)=[O:19])=[CH:13][CH:12]=1>O1CCCC1>[C:11]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:12]=[CH:13][C:14]([CH2:17][C:18]([C:7]2[S:6][CH:10]=[CH:9][N:8]=2)=[O:19])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 9256ThiazoleHCID 17815837N-methoxy-N-methyl-4-biphenylacetamideHCID 178418918HCID 178418918, compound

Product 1

HCID 594966612-Biphenyl-4-yl-1-(1,3-thiazol-2-yl)ethanoneYield 62.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-10 °C

Procedure

2.0 M of Isopropylmagnesium chloride in tetrahydrofuran (0.24 mL) was added to a solution of 1,3-thiazole (40 mg, 0.47 mmol) in tetrahydrofuran (6 mL) at −78° C. The reaction was stirred for 1 h. as it was warmed to −10° C. 2-Biphenyl-4-yl-N-methoxy-N-methylacetamide (100 mg, 0.4 mmol) in Tetrahydrofuran (2 mL) was added dropwise at −10° C. The reaction was stirred for 2 h. while the reaction was warmed to r.t. gradually. The reaction was quenched with saturated NH4Cl, and was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the crude product, which was purified by Flash chromatography on a silica gel column (EtOAc:Hexane, 1:3 to 1:1) gave the 2-biphenyl-4-yl-1-(1,3-thiazol-2-yl)ethanone (70 mg, 60%) as a white solid. Analytical LCMS (M+H)+: m/z=279.9.

Workup

  1. stirringThe reaction was stirred for 2 h. while the reaction
  2. temperaturewas warmed to r.t. gradually
  3. customThe reaction was quenched with saturated NH4Cl
  4. extractionwas extracted with ethyl acetate
  5. washThe organic phase was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give the crude product, which
  10. customwas purified by Flash chromatography on a silica gel column (EtOAc:Hexane, 1:3 to 1:1)

Sources & evidence

ORD record
ord-f9be290352eb4c419e8157f181e9ac71
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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